Dye-forming coupler, silver halide photographic light-sensitive material and azomethine dye compound

Abstract

A yellow dye-forming coupler represented by formula (I): wherein Q represents a group of nonmetallic atoms that form a 5- to 7-membered ring in combination with the —N═C—N(R 1 )—; R 1 and R 2 each represent a substituent; R 4 represents an alkyl group; m represents an integer of 0 to 4; and X represents a hydrogen atom, or a group capable of being split-off upon a coupling reaction with an oxidized product of a developing agent; and when R 4 represents a primary alkyl group, R 1 represents —(CH 2 ) 3 O—R 101 in which R 101 is an alkyl group having 4 to 8 carbon atoms. A silver halide color photographic light-sensitive material having at least one yellow dye-forming coupler represented by formula (I) in at least one layer provided on a support.

1. A compound represented by formula (I): 
       
         
           
           
               
               
           
         
         wherein Q represents a group represented by —C(—R 11 )═C(R 12 )—SO 2 —; wherein R 11  and R 12  bond with each other to form, together with the —C══C— moiety, a 5- to 7-membered ring, or R 11  and R 12  each independently represents a hydrogen atom or a substituent; 
         R1 represents a substituent; 
         R3 represents a substituent; 
         R4 represents a substituent; 
         m represents an integer of 0 to 4; wherein when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring; and 
         X represents a hydrogen atom, or a group capable of being split-off upon a coupling reaction with an oxidized product of a developing agent; 
         with the proviso that the following compound (I-A) is excluded from the dye-forming coupler represented by formula (I): 
       
       
         
           
           
               
               
           
         
       
     
     
       2. The compound as claimed in  claim 1 , wherein R1 is a substituted or unsubstituted alkyl group, and R3 is a halogen atom, an alkoxy group, an aryloxy group, an alkyl group, an alkylthio group, or an arylthio group. 
     
     
       3. The compound as claimed in  claim 1 , wherein the substituent represented by R1 has 11 or more carbon atoms in total. 
     
     
       4. The compound as claimed in  claim 1 , wherein X is an imidazole-1-yl group which may have a substituent, a pyrazole-1-yl group which may have a substituent, or a pyrrole-1-yl group which may have a substituent. 
     
     
       5. A compound represented by formula (II): formula (II) 
       
         
           
           
               
               
           
         
         wherein R1 represents a substituent; 
         R2 represents a substituent; 
         I represents an integer of 0 to 4; wherein when I is 2 or more, R2s may be the same or different, or R2s may bond with each other to form a ring; 
         R3 represents a substituent; 
         R4 represents a substituent; 
         m represents an integer of 0 to 4; wherein when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring; and 
         Y represents a group capable of being split off upon a coupling reaction with an oxidized product of a developing agent; 
         with the proviso that the following compound (I-A) is excluded from the dye-forming coupler represented by formula (II): 
       
       
         
           
           
               
               
           
         
       
     
     
       6. The compound as claimed in  claim 5 , wherein R1 is a substituted or unsubstituted alkyl group, and R3 is a halogen atom, an alkoxy group, an aryloxy group, an alkyl group, an alkylthio group, or an arylthio group. 
     
     
       7. The compound as claimed in  claim 5 , wherein the substituent represented by R1 has 11 or more carbon atoms in total. 
     
     
       8. The compound as claimed in  claim 5 , wherein Y is an imidazole-1-yl group which may have a substituent, a pyrazole-1-yl group which may have a substituent, or a pyrrole-1-yl group which may have a substituent. 
     
     
       9. A compound represented by formula (I-2): 
       
         
           
           
               
               
           
         
         wherein Q1 represents a group represented by —C(—R 11 )═C(R 12 )-Z-; wherein Z represents —SO 2 — or —CO—; and R 11  and R 12  bond with each other to form, together with the —C═C— moiety, a 5 to 7-membered ring, or R 11  and R 12  each independently represents a hydrogen atom or a substituent; 
         R1 represents a substituent; 
         R3 represents a substituent; 
         R4 represents a substituent; 
         m represents an integer of 0 to 4; wherein when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring; and 
         X1 represents a group that has thereon a dissociation group whose pKa is 1 to 12, and that is capable of being split-off upon a coupling reaction with an oxidized product of a developing agent. 
       
     
     
       10. The compound as claimed in  claim 9 , wherein R1 is a substituted or unsubstituted alkyl group, and R3 is a halogen atom, an alkoxy group, an aryloxy group, an alkyl group, an alkylthio group, or an arylthio group. 
     
     
       11. The compound as claimed in  claim 9 , wherein the substituent represented by R1 has 11 or more carbon atoms in total. 
     
     
       12. The compound as claimed in  claim 9 , wherein X1 is an imidazole-1-yl group which may have a substituent, a pyrazole-1-yl group which may have a substituent, or a pyrrole-1-yl group which may have a substituent. 
     
     
       13. An azomethine dye compound represented by formula (D): 
       
         
           
           
               
               
           
         
         wherein, in formula (D), Q represents a group represented by —C(—R 11 )═C(—R 12 )—SO 2 —; wherein R 11  and R 12  bond with each other to form, together with the —C═C— moiety, a 5- to 7 membered ring, or R 11  and R 12  each independently represents a hydrogen atom or a substituent; 
         R1 represents a substituent; 
         R3 represents a substituent; 
         R4 represents a substituent; 
         m represents an integer of 0 to 4; wherein when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring; 
         R5 and R6 each independently represents a hydrogen atom or a substituent, or R5 and R6 may bond with each other to form a ring; 
         R7 represents a substituent; 
         n represents an integer of 0 to 4; wherein when n is 2 or more, R7s may be the same or different, or R7s may bond with each other to form a fused ring; or when n is 1 or more, R7 may bond with R5 or R6 to form a fused ring; 
         with the proviso that at least one group selected from the group consisting of R1, R3, and R4 is a group having 7 to 50 carbon atoms in total. 
       
     
     
       14. The azomethine dye compound as claimed in  claim 13 , wherein R1 is a substituted or unsubstituted alkyl group, and R3 is a halogen atom, an alkoxy group, an aryloxy group, an alkyl group, an alkylthio group, or an arylthio group. 
     
     
       15. An azomethine dye compound represented by formula (IV), wherein an angle that is defined by a dihedral angle C*1 N*2 C*3 C*4 and that is the most stabilized stereochemical structure in terms of energy, which is measured by quantum chemistry calculations, is within the range between −28° and 28°: 
       
         
           
           
               
               
           
         
         wherein, in formula (IV), *1, *2, *3 and *4 each expresses a number labeled on the atom and define the angle represented by the dihedral angle C*1 N*2 C*3 C*4; 
         R3 and R4 each independently represents a substituent; 
         m represents an integer of 0 to 4; wherein when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring; 
         R5 and R6 each independently represents a hydrogen atom or a substituent, or R5 and R6 may bond with each other to form a ring; 
         R8 represents an aryl group or a heterocyclic group; 
         with the proviso that at least one group selected from the group consisting of R3, R4, and at least one substituent on the aryl ring or heterocycle represented by R8, is a group having 10 or more carbon atoms in total; and that the calculation based on quantum chemistry, which is used to measure the dihedral angle C*1 N*2 C*3 C*4 is carried out using the basis function of 6–31 or more according to a widely used B3LYP method (density-functional method). 
       
     
     
       16. The azomethine dye compound as claimed in  claim 15 , wherein R8 is a group represented by formula (V): 
       
         
           
           
               
               
           
         
         wherein, in formula (V), Q represents a group represented by —C(—R 11 )═C(—R 12 )—SO 2 —; wherein R 11  and R 12  bond with each other to form, together with the —C═C— moiety, a 5- to 7-membered ring, or R 11  and R 12  each independently represents a hydrogen atom or a substituent; 
       
       and R1 represents a substituent. 
     
     
       17. A compound represented by formula (I-2): 
       
         
           
           
               
               
           
         
         wherein Q1 represents a group represented by —C(—R 11 )═C(R 12 )-Z-; wherein Z represents —SO 2 — or —CO—; and R 11  and R 12  bond with each other to form, together with the —C═C— moiety, a 5 to 7-membered ring, or R 11  and R 12  each independently represents a hydrogen atom or a substituent; 
         R1 represents a substituent; 
         R3 represents a substituent; 
         R4 represents a substituent; 
         m represents an integer of 0 to 4; wherein when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring; and 
         X1 represents a group that has thereon a dissociation group whose pKa is 1 to 12, and that is capable of being split-off upon a coupling reaction with an oxidized product of a developing agent, 
         provided that the compound represented by formula (I-2) satisfies any one of the following conditions 1) to 3): 
         1) Z represents —SO 2 —, 
         2) the number of carbon atoms in R1 is 11 or more in total, 
         3) X1 represents a group that has thereon a dissociation group whose pKa is 1 to 12, and that is capable of being split-off with an oxygen atom or sulfur atom, upon coupling reaction with an oxidized product of a developing agent; or X1 represents a group that has thereon a dissociation group whose pKa is 1 to 12, that is capable of split-off with a nitrogen atom, upon coupling reaction with an oxidized product of a developing agent, and that is selected from the group consisting of a 5- to 7-membered saturated or nonaromatic heterocycle, an imidazole-1-yl which may have a substituent, a pyrazole-1-yl which may have a substituent, a pyrrole-1-yl which may have a substituent, a 6-membered aromatic heterocyclic group, a carbonamido group, a sulfonamido group, an arylazo group and a carbamoylamino group. 
       
     
     
       18. The azomethine dye compound as claimed in  claim 9 , wherein said dissociation group in X1 is selected from the group consisting of a —COOH group, a —NHSO 2 — group, a phenolic hydroxyl group, a —CONHCO— group, a —CONHSO 2 — group, a —CONHSO 2 NH 2  group, and a —SO 2 NHSO 2 — group. 
     
     
       19. The compound as claimed in  claim 17 , wherein said dissociation group in X1 is selected from the group consisting of a —COOH group, a —NHSO 2 — group, a phenolic hydroxyl group, a —CONHCO— group, a —CONHSO 2 — group, a —CONHSO 2 NH 2  group, and a —SO 2 NHSO 2 — group. 
     
     
       20. The compound as claimed in  claim 1 , which is a dye-forming coupler. 
     
     
       21. The compound as claimed in  claim 5 , which is a dye-forming coupler. 
     
     
       22. The compound as claimed in  claim 9 , which is a dye-forming coupler.